What not to do when owing taxes

Filing a tax extension feels stressful for many business owners. Missing numbers, unfinished bookkeeping, and uncertainty about the tax bill can make tax season overwhelming. But filing an extension (in many cases) can be the smartest move you can make.

A tax extension gives you more time to file your return so you can organize your records, receive missing documents like K-1s, and avoid rushing through a return that could contain mistakes. In this episode, we break down how extensions actually work, clear up common myths about audit risk, and explain what to do if you cannot afford your tax bill.

We also cover why ignoring the IRS is the worst move you can make, how penalties work, and the payment plan options available to business owners who need more time to pay what they owe.

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Chapters

(02:30) Key Tax Deadlines Every Business Owner Should Know
Partnerships and S corporations file by March 15. Personal returns and C corporations file by April 15.

(04:00) What a Tax Extension Actually Means
A tax extension gives you more time to file your return, but your taxes are still due by the original deadline.

(05:30) Common Myths About Filing a Tax Extension
Extensions do not increase audit risk, and many high income taxpayers file them every year.

(07:00) The Most Common Reasons Business Owners File Extensions
Unfinished bookkeeping, waiting on K-1 forms, or planning opportunities like retirement contributions or cost segregation.

(11:00) The Cost of Not Filing Your Tax Return
Failure to file penalties can reach hundreds of dollars per owner per month for business entities.

(13:00) Why You Should Still Estimate and Pay Taxes With an Extension
Making an estimated payment reduces penalties and interest if you expect to owe.

(15:30) What to Do If You Cannot Afford Your Tax Bill
The IRS offers short term payment plans, installment agreements, and other options if you communicate.

(20:00) Key Takeaways
Tax extensions are not a red flag. Used correctly, they give business owners time to plan, reduce mistakes, and stay in control of their tax situation.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
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🎙 ABOUT THE PODCAST
The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.